Daniel C.S. Powell allegedly blew $5,000 of investor funds on cowboy boots. But that’s not the only reason he’s being financially regulated this week. Also problematic, from a technical regulatory standpoint, was that he “spent the past seven years creating the illusion that [he ran] a legitimate company involved in the life settlement industry,” says the SEC. He then used this illusion to raise $4.5 million from investors, but never “purchased or generated any revenue as a result of brokering the sale of a single life settlement.”

Instead, Powell upgraded his footwear and spent $5,000 to register for a dating service. He then blew $212,000 on cars, $240,000 in cash and checks, and $290,000 in personal debit card transactions before turning, as many wealthy people do, to philanthropy: he made a $55,000 donation to a tribute of Michael Jackson and a $35,000 donation to rapper Usher’s New Look Foundation. Of the $4.5 million raised, only $29,396.55 remains in his bank accounts.